Publication detail

Study of rearrangement of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones to 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles.

Authors: Hanusek Jiří | Kammel Richard | Hladíková Veronika | Marek Lukáš

Year: 2017

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Study of rearrangement of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones to 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles.	Recently we have observed unexpected behavior during the reaction of 3-bromo-1,3-dihydro-2H-indol-2-one (3-bromo-oxindole, 1a) with 4-methoxythiobenzamide giving a product arising from a Eschenmoser coupling reaction i.e. (3Z)-3-[amino(4-methoxyphenyl)-methylidene]-1,3-dihydro-2H-indol-2-one instead of the expected transformation product 5-(2-aminophenyl)-4-hydroxy-2-(4-methoxyphenyl)-1,3-thiazole. Deeper exploration4 of this reaction involving various substituted thiobenzamides has shown that the expected thiazole is formed first (kinetic control) but it is unstable and under thermodynamic control conditions rearranges to Eschenmoser coupling product (Scheme for R2 = H). In this work the influence of further substitution (R2) in starting 3-bromo-oxindole will be discussed due to potential application of this synthetic protocol for the preparation of highly effective kinase inhibitors1 (2H-indol-2-ones) and and/or fluorescent materials (thiazoles).

Search